Injury‐Triggered Blueing Reactions of <i>Psilocybe</i> “Magic” Mushrooms

Lenz, Claudius; Wick, Jonas; Braga, Daniel; García‐Altares, María; Lackner, Gerald; Hertweck, Christian; Gressler, Markus; Hoffmeister, Dirk

doi:10.1002/ange.201910175

Cited by 19 publications

(16 citation statements)

References 43 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…This difference may be due to a disruption of the cellular structure of the fungus, which occurred due to the splitting of the mushroom into analogous parts that were used for various types of processing. Disruption of the cell structure may lead to faster degradation of tryptamines due to hydrolysis to psilocin and subsequent oxidation to quinoid dyes 55,56 . This hypothesis was confirmed by the fact that almost immediately after cutting, the fresh fruiting body turned blue.…”

Section: Resultsmentioning

confidence: 86%

“…The degradation of psilocybin may be due to the gradual biotransformation of the sliced specimens since psilocybin is dephosphorylated enzymatically by phosphatase to psilocin, which is unstable because of it being readily subjected to oxidation to blue quinoid dye 55,56 . Significant blue staining was observed for the chopped fresh mushroom samples only a few seconds after the fruiting bodies were cut.…”

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Stability of psilocybin and its four analogs in the biomass of the psychotropic mushroom Psilocybe cubensis

Gotvaldová

Hájková

Borovička

et al. 2020

Drug Testing and Analysis

View full text Add to dashboard Cite

Psilocybin, psilocin, baeocystin, norbaeocystin, and aeruginascin are tryptamines structurally similar to the neurotransmitter serotonin. Psilocybin and its pharmacologically active metabolite psilocin in particular are known for their psychoactive effects. These substances typically occur in most species of the genus Psilocybe (Fungi, Strophariaceae). Even the sclerotia of some of these fungi known as “magic truffles” are of growing interest in microdosing due to them improving cognitive function studies. In addition to microdosing studies, psilocybin has also been applied in clinical studies, but only its pure form has been administrated so far. Moreover, the determination of tryptamine alkaloids is used in forensic analysis. In this study, freshly cultivated fruit bodies of Psilocybe cubensis were used for monitoring stability (including storage and processing conditions of fruiting bodies). Furthermore, mycelium and the individual parts of the fruiting bodies (caps, stipes, and basidiospores) were also examined. The concentration of tryptamines in final extracts was analyzed using ultra‐high‐performance liquid chromatography coupled with mass spectrometry. No tryptamines were detected in the basidiospores, and only psilocin was present at 0.47 wt.% in the mycelium. The stipes contained approximately half the amount of tryptamine alkaloids (0.52 wt.%) than the caps (1.03 wt.%); however, these results were not statistically significant, as the concentration of tryptamines in individual fruiting bodies is highly variable. The storage conditions showed that the highest degradation of tryptamines was seen in fresh mushrooms stored at −80°C, and the lowest decay was seen in dried biomass stored in the dark at room temperature.

show abstract

Section: Resultsmentioning

confidence: 86%

Section: Resultsmentioning

confidence: 99%

Stability of psilocybin and its four analogs in the biomass of the psychotropic mushroom Psilocybe cubensis

Gotvaldová

Hájková

Borovička

et al. 2020

Drug Testing and Analysis

View full text Add to dashboard Cite

show abstract

“…The extended washing process was tedious given the reactive nature of psilocin, which is highly prone to degradation and forming blue oxidation products. 23 The phosphorylation was accomplished at stage 4a by the reaction of tetrabenzylpyrophosphate (TBPP) with the lithium phenolate of 4 using n -butyllithium under cryogenic conditions. The reaction also produced 1 equiv of lithium dibenzylphosphate as a byproduct.…”

Section: Resultsmentioning

confidence: 99%

“…The extended washing process was tedious given the reactive nature of psilocin, which is highly prone to degradation and forming blue oxidation products. 23 …”

Section: Resultsmentioning

confidence: 99%

Direct Phosphorylation of Psilocin Enables Optimized cGMP Kilogram-Scale Manufacture of Psilocybin

et al. 2020

View full text Add to dashboard Cite

A second-generation kilogram-scale synthesis of the psychedelic tryptamine psilocybin has been developed. The synthesis was designed to address several challenges first encountered with the scale-up of previously described literature procedures, which were not optimized for providing consistent yield and purity of products, atom economy, or being run in pilot plant-scale reactors. These challenges were addressed and circumvented with the design of the second-generation route, which featured an optimized cGMP large-scale Speeter–Anthony tryptamine synthesis to the intermediate psilocin with improved in-process control and impurity removal over the three steps. Psilocin was subsequently phosphorylated directly with phosphorous oxychloride for the first time, avoiding a tedious and poor atom economy benzyl-protecting group strategy common to all previously described methods for producing psilocybin. In this report, the challenges encountered in a 100 g scale first-generation literature-based synthesis are highlighted, followed by a detailed description of the newly developed second-generation synthesis to provide over one kilogram of high-purity psilocybin under cGMP.

show abstract

“…The transcriptional analysis of the recently identified biosynthetic genes confirms its fruiting body-specific production (R et al 2020). The blueing reaction of psilocybin-producing fruiting bodies upon injury has recently been demonstrated to be due to enzyme-mediated oxidative oligomerization of psilocybin suggesting that at least part of the defense function of this compound may be based on optical deterrence (Lenz et al 2020). Wound-activation by injury (oxidation) has been reported for other secondary metabolites of Agaricomycete fruiting bodies (Stadler and Sterner 1998;P 2008) but the genetic basis of these compounds and reactions is often not known.…”

Section: Defensementioning

confidence: 99%

Lessons on fruiting body morphogenesis from genomes and transcriptomes of Agaricomycetes

Nagy

Vonk

Künzler

et al. 2021

Preprint

View full text Add to dashboard Cite

Fruiting bodies of mushroom-forming fungi (Agaricomycetes) are among the most complex structures produced by fungi. Unlike vegetative hyphae, fruiting bodies grow determinately and follow a genetically encoded developmental program that orchestrates tissue differentiation, growth and sexual sporulation. In spite of more than a century of research, our understanding of the molecular details of fruiting body morphogenesis is limited and a general synthesis on the genetics of this complex process is lacking. In this paper, we aim to comprehensively identify conserved genes related to fruiting body morphogenesis and distill novel functional hypotheses for functionally poorly characterized genes. As a result of this analysis, we report 921 conserved developmentally expressed gene families, only a few dozens of which have previously been reported in fruiting body development. Based on literature data, conserved expression patterns and functional annotations, we provide informed hypotheses on the potential role of these gene families in fruiting body development, yielding the most complete description of molecular processes in fruiting body morphogenesis to date. We discuss genes related to the initiation of fruiting, differentiation, growth, cell surface and cell wall, defense, transcriptional regulation as well as signal transduction. Based on these data we derive a general model of fruiting body development, which includes an early, proliferative phase that is mostly concerned with laying out the mushroom body plan (via cell division and differentiation), and a second phase of growth via cell expansion as well as meiotic events and sporulation. Altogether, our discussions cover 1480 genes of Coprinopsis cinerea, and their orthologs in Agaricus bisporus, Cyclocybe aegerita, Armillaria ostoyae, Auriculariopsis ampla, Laccaria bicolor, Lentinula edodes, Lentinus tigrinus, Mycena kentingensis, Phanerochaete chrysosporium, Pleurotus ostreatus, and Schizophyllum commune, providing functional hypotheses for ~10% of genes in the genomes of these species. Although experimental evidence for the role of these genes will need to be established in the future, our data provide a roadmap for guiding functional analyses of fruiting related genes in the Agaricomycetes. We anticipate that the gene compendium presented here, combined with developments in functional genomics approaches will contribute to uncovering the genetic bases of one of the most spectacular multicellular developmental processes in fungi. Key words: functional annotation; comparative genomics; cell wall remodeling; development; fruiting body morphogenesis; mushroom; transcriptome

show abstract

Injury‐Triggered Blueing Reactions of Psilocybe “Magic” Mushrooms

Cited by 19 publications

References 43 publications

Stability of psilocybin and its four analogs in the biomass of the psychotropic mushroom Psilocybe cubensis

Stability of psilocybin and its four analogs in the biomass of the psychotropic mushroom Psilocybe cubensis

Direct Phosphorylation of Psilocin Enables Optimized cGMP Kilogram-Scale Manufacture of Psilocybin

Lessons on fruiting body morphogenesis from genomes and transcriptomes of Agaricomycetes

Contact Info

Product

Resources

About